Studies on the chemistry and reactivity of alpha-substituted ketones in isonitrile-based multicomponent reactions.
Using the Passerini and Ugi reactions as representative tests, the utility of several alpha-substituted ketones R-CO-CH(2)-X (X = sulfonyloxy, acyloxy, azido, halo, hydroxy, and sulfonyl) in isonitrile-based multicomponent reactions was explored. In a relative rate study (R = PhCH(2)CH(2)), each of the alpha-substituted ketones underwent Passerini condensation more rapidly than the parent ketone. Short, highly convergent routes to oxazoline, beta-lactam, di-O-acylglyceramides, and other molecular frameworks were developed.
Fan
Lijun
L
Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
Adams
Ashley M
AM
Polisar
Jason G
JG
Ganem
Bruce
B
D002850:Chromatography, Gel; D002855:Chromatography, Thin Layer; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*; D014961:X-Ray Diffraction; D047090:beta-Lactams / Q000737:chemistry
D007202:Indicators and Reagents; D007659:Ketones; D009570:Nitriles; D047090:beta-Lactams